Chloro(diphenyl)silane → 2-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

HRID 30250

反応式

HRID 30250 の反応式
[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([CH:11](O)[C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[SiH](C1C=CC=CC=1)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 74206Chloro(diphenyl)silaneHCID 516892Sodium BicarbonateHCID 1317270292-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalen-7-ol

生成物 1

HCID 1317270302-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

The product from step f) (300 mg, 0.69 mmol) in dichloroethane (2.6 ml) was treated with InCl3 (153 mg, 0.69 mmol) and chlorodiphenylsilane (457 mg, 2.08 mmol). The contents were heated to 60° C. for 16 hours. The reaction mixture was cooled to 22° C., poured into sat. NaHCO3 and diluted with EtOAc (75 ml); producing a white emulsion. The emulsion was passed through celite and the organic layer was separated, washed with brine (25 ml) and dried (MgSO4). The crude product was dissolved in 7:3 hexanes:EtOAc and passed through a plug of silica gel to give the subtitle compound. MS calculated for C16H15Br2NS+H 414, observed 412, 414, 416.

後処理

  1. temperatureThe reaction mixture was cooled to 22° C.
  2. customproducing a white emulsion
  3. customthe organic layer was separated
  4. washwashed with brine (25 ml)
  5. dry with materialdried (MgSO4)
  6. dissolutionThe crude product was dissolved in 7:3 hexanes

出典と根拠

ORDレコード
ord-de128afaab06408dbc1978e553987d92
出典データセット
uspto-grants-2008_09
特許番号
US07423056B2

関連ノート

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